Often the only way to make sure a startup stays funded is by focusing on building and testing features as quickly as possible. However, when the product and the business model have been validated, you are moving into a state where you need to keep your tech debt under control, both to be able to keep delivering features at a high speed, and to make sure your service has high availability and a good security level. This often seems to co-occur with hiring of a new CTO. How can you deal with this situation?
Often the gut feeling of the engineers in these organizations is to stop delivering features and start a full rewrite. This is high risk, and potentially a very expensive approach. There are no simple solutions for this problem, also it cannot be dealt with inside the tech organization, alone.
You need to build an understanding in management and engineering on how he product will be a continuous changing and developing “organism” that will never be finished. At the same time you need to ensure that the engineering culture and work processes support you in where you want to go.